Phase change ink formulations, colorant formulations, and methods of forming colorants

ABSTRACT

The invention encompasses a compound having the formula:  
                 
 
     wherein R 1 , Z and the carbonyl can be comprised by a common ring, wherein R 1  comprises a chromophore that absorbs light from the visible wavelength range, and wherein n is an integer that is at least 12. The invention also encompasses a solid phase change ink composition. Such composition includes a phase change ink carrier and a colorant. The colorant comprises a chromophore that absorbs light from the visible wavelength range, and has the formula:  
                 
 
     wherein R 1 , Z and the carbonyl can be comprised by a common ring, wherein n is an integer that is at least 12. Additionally, the invention encompasses a method of forming a colorant. A first compound having the formula,  
                 
 
     is reacted with a second compound having the formula Z(CH 2 ) n CH 3 , wherein n is an integer that is at least 12, to form a third compound having the formula,  
                 
 
     wherein the third compound comprises a chromophore that absorbs light from the visible wavelength range.

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application is a continuation-in-part application of U.S.patent application Ser. No. 09/023,851, filed on Feb. 13, 1998; which isin turn a continuation-in-part application of U.S. patent applicationSer. No. 08/672,815 (now U.S. Pat. No. 5,830,942), filed Jun. 28, 1996,and Ser. No. 09/013,410, filed Jun. 28, 1996.

BACKGROUND OF THE INVENTION

[0002] 1. Field of the Invention

[0003] The invention relates to new colorant compositions, and tomethods of forming and using such colorants. In particular applications,the invention pertains to phase change ink formulations.

[0004] 2. Description of the Relevant Art

[0005] The present invention encompasses new colorant compounds, routesto their preparation, and methodology for incorporating such compoundsinto phase change inks. Phase change inks are compositions which are ina solid phase at ambient temperature, but which exist in a liquid phaseat an elevated operating temperature of an ink jet printing device. Atthe jet operating temperature, droplets of liquid ink are ejected fromthe printing device. When the ink droplets contact the surface of aprinting media, they solidify to form a printed pattern. Phase changeink methodology is described generally in U.S. Pat. Nos. 4,889,560;5,372,852 and 5,827,918.

[0006] A definition which will be adopted in this disclosure and theclaims that follow will be to utilize the term “colorant” to refer tomodified dyes, chromophores and pigments which are suitable forinclusion in phase change inks. Another definition which will be adoptedin this disclosure and the claims that follow will be to refer to aphase change ink composition as comprising a colorant and a carrier. Theterm “carrier” is to be understood to comprise all components of a phasechange ink composition with the exception of the colorant. In phasechange ink compositions comprising more than one colorant, the carrierwill include everything except a particular colorant of interest, andcan, therefore, comprise colorants other than that which is of interest.

[0007] A difficulty associated with phase change inks can be insolubilizing traditionally utilized dyes, chromophores and pigments.Many colored compounds useful in producing phase change inks for digitalprinting generally comprise polar functional groups, and accordingly areinsoluble in the organic carrier of a phase change ink composition. Thesolubility of the colored compounds can be improved by increasing thehydrophobic character of the colored compounds. Accordingly, it isdesirable to develop methods for increasing the hydrophobic character ofexisting chromophores, dyes and pigments to produce new coloredcompounds, as well as to develop new colorants with substantialhydrophobic character.

BRIEF SUMMARY OF THE INVENTION

[0008] In one aspect, the invention encompasses a compound having theformula:

[0009] wherein R₁ comprises a chromophore that absorbs light from thevisible wavelength range, and wherein n is an integer that is at least12.

[0010] In another aspect, the invention encompasses a solid phase changeink composition. Such composition includes a phase change ink carrierand a colorant. The colorant comprises a chromophore that absorbs lightfrom the visible wavelength range, and has the formula:

[0011] wherein n is an integer that is at least 12.

[0012] In yet another aspect, the invention encompasses a method offorming a colorant. A first compound having the formula,

[0013] is reacted with a second compound having the formulaZ(CH₂)_(n)CH₃, wherein n is an integer that is at least 12, to form athird compound having the formula,

[0014] wherein the third compound comprises a chromophore that absorbslight from the visible wavelength range and is soluble in a phase changeink.

BRIEF DESCRIPTION OF THE DRAWINGS

[0015]FIG. 1 shows a generalized reaction scheme comprising methodologyof the present invention.

[0016]FIG. 2 shows a generalized reaction scheme of a net overallreaction comprising methodology of the present invention.

[0017]FIG. 3 shows yet another generalized reaction scheme of a netoverall reaction comprising methodology of the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The invention comprises new colorants, as well as new phasechange ink compositions comprising the colorants. The new colorants havea substantial amount of hydrophobic character. In one aspect, thehydrophobic character is imparted by incorporating at least one alkyl oralkoxylate chain that is at least 13 carbon units long into colorants ofthe present invention. In particular embodiments, the alkyl oralkoxylate chain is at least 20 carbon units long, and in otherembodiments at least 40 carbon units long. It can be preferred that thenumber of carbon atoms in the alkyl or alkoxylate chain not exceed about300, as such long carbon chains (if present in sufficient concentration)can increase a melting point of a phase change ink beyond a desiredlimit of about 170° C. Of course, if a colorant is provided to asufficiently low concentration in a phase change ink such that carbonchains comprising greater than 300 carbon units do not adversely affecta melting point of the ink, the preferability of having less than 300carbon units is diminished. Also, it is noted that eutectic mixturescomprising a colorant can lower a melting point of the colorant so thata melting point of the colorant can be less than or equal to 170°C. evenif the colorant has chains with more than 300 carbon units.Consequently, it is noted that a melting point temperature of a phasechange ink can be engineered even from colorants having melting pointssignificantly different than that ultimately desired in the phase changeink.

[0019] A general formula for one class of colorant encompassed by thepresent invention is shown below as compound 1.

[0020] The group R₁ of compound 1 comprises a chromophore that absorbslight from the visible wavelength range (i.e., light having a wavelengthof from about 400 nanometers to about 750 nanometers). The label n ofcompound 1 represents an integer that is at least 12. In preferredembodiments, n is at least 17. In further preferred embodiments(particularly where the colorant is provided in high concentration in aphase change ink, with high concentration being defined as aconcentration greater than about 25% (by weight) of the ink), n is lessthan or equal to 299. The segment Z of compound 1 comprises one or moreatoms; and comprises an atom selected from group IV of the periodictable (i.e., the group comprising carbon), group V of the periodic table(i.e., the group comprising nitrogen) or group VI of the periodic table(i.e., the group comprising oxygen and sulphur).

[0021] Although the compound 1 is shown in a linear form, it is to beunderstood that compound 1 can be comprised by a cyclic structure (i.e.,compound 1 can be a portion of a cyclic structure), and that thecarbonyl, R₁ and Z can be contained in a common ring of such cyclicstructure. Compound 1A shows a dashed line to indicate the ring of acyclic structure of compound 1.

[0022] In particular embodiments, the segment Z(CH₂)_(n)CH₃ of compound1 is either group 2 (below) or group 3 (below).

NH(CH₂)_(n)CH₃   2.

CH₃(CH₂)_(n)—N—(CH₂)_(y)CH₃   3.

[0023] In group 3, the label y is an integer that can be the same ordifferent than n, and which is preferably greater than 12, although itcan be zero. The amines (or generally a nucleophile) of groups 2 and 3correspond to the component Z of compound 1.

[0024] The segment R₁ of compound 1 comprises carbon, and can comprise,for example, aryl moieties in color-yielding combinations. Exemplaryaryl moieties are phenyl and naphthyl. The segment R₁ and the carbonylof compound 1 can together comprise a chemical group selected from thegroup consisting of ester, lactone, amide, lactam and imide. Further, R₁and the carbonyl of compound 1 can together comprise an auxochrome. Thegroup R₁ can also comprise an auxochrome by itself by containingelectron donating groups or electron withdrawing groups.

[0025] Further, the group R₁ of compound 1 preferably comprises achromophore that absorbs light within the visible wavelength range suchthat compound 1 can be a suitable colorant for a phase change ink. Amongthe preferred chromophores for phase change inks are chromophorescorresponding to cyan, magenta, yellow or black colors. The chromophoreencompassed by the compound 1 can comprise, for example, methine, metalphthalocyanine, metal phthalocyanine, azamethine, azo, triphenylmethane,rhodamine, xanthene, indoaniline, pyridone, perylene, anthrapyridone andanthraquinone.

[0026] In an exemplary embodiment, compound 1 can have a formulacorresponding to that of compound 4 (shown below).

[0027] The components R₅₀, R₅₁, R₅₂, and R₅₃ of compound 4 can, forexample, be selected from the group consisting of hydrogen, halogens,hydroxy groups, alkoxy groups, trifluoromethyl groups, and alkyl groups,and can be the same as one another or different than one another. Thecomponents R₇ and R₈ of compound 4 are selected from the groupconsisting of hydrogen and carbon-containing materials, and can be, forexample, alkyl moieties, aryl moieties or hydrogen. Components R₇ and R₈can be the same or different relative to one another, and can becomprised by a common ring. In particular embodiments, at least one ofthe components R₇ and R₈ of compound 4 can comprise a chain having theformula of material 5.

[0028] In material 5, j is an integer of from 0 to about 300 (preferablyfrom 0 to 100, and more preferably from 1 to 10), and the representationof “(Q, H)” indicates that either a substituent Q or a hydrogen can bein the shown positions. Substituent Q represents either an alkyl groupor an aryl group, and can vary amongst different alkyl and aryl groupswithin either or both of components R₇ and R₈. In particularembodiments, Q is CH₃ throughout both of R₇ and R₈.

[0029] A compound corresponding to compound 4, and having R₇ and R₈corresponding to the formula of material 5, can be formed according tothe reaction scheme shown in FIG. 1. Specifically, aniline isalkoxylated to yield aniline 252 (shorthand for aniline with 2 moles ofethylene oxide (EO), 5 moles of propylene oxide (PO) and 2 moles of EOto yield a block co-polymer). The aniline 252 of FIG. 1 corresponds to acombination of aniline and a pair of polymers encompassed by material 5,with the polymer encompassed by material 5 having the formula shownbelow as 5A (i.e., a 1:2.5:1 structure).

[0030] The 2.5 of material 5A indicates that on average there are 2.5 ofthe CH₂CH(CH₃)O units in a chain. Of course, in any given chain, theactual number of such units will be an integer amount (typically 2 or3).

[0031] After formation of the aniline 252 in the FIG. 1 reactionprocess, the aniline 252 is acetylated. After the acetylation, aresulting aniline 252 diacetate is converted to an aldehyde by aVilsmeier-Haack reaction utilizing phosphorus oxychloride andN,N-dimethylformamide (DMF). Basic hydrolysis of the acetate protectinggroups is accomplished with warm dilute sodium hydroxide containing asmall percentage of potassium hydroxide. The benzaldehyde derivativecontaining the free hydroxyl groups on the alkoxylate chain isneutralized, phased by warming to above the cloud point, and allowed tostand and separate. The salt layer is removed and the resulting aldehydelayer is reduced in vacuo to yield the anhydrous precursor of achromophore. The aldehyde is then condensed with a cyanoacetatederivative to form the resulting exemplary colorant of the presentinvention.

[0032] Other epoxides can be utilized instead of, or in addition to, theEO and PO epoxides discussed above. For instance, butylene oxide (BO)and/or styrene oxide (SO) can also be utilized.

[0033] The reaction chemistry shown in FIG. 1 is an example of acondensation reaction encompassed by the present invention. A moregeneral description of condensation reactions of the present inventionis a follows. First, a starting material 10 (shown below, and referredto hereafter as “compound 10”) is provided.

[0034] The segment A of compound 10 is an aromatic ring, and the groupR₄ of compound 10 comprises one or both of carbon and hydrogen. Compound10 is reacted with a cyanoacetate derivative 11 having the formula shownbelow.

[0035] The label “n” of cyanoacetate derivative 11 represents aninteger, and is preferably at least 12.

[0036] Condensation of aldehyde compound 10 with cyanoacetate derivative11 forms a product having formula 12.

[0037] Compound 12 is a methine colorant, and an exemplary compoundencompassed by the present invention. In a particular embodiment of theinvention, compound 11 comprises a stearyl amide of cyanoacetic acid,and compound 10 comprises N,N-dialkyl amino benzaldehyde. Condensationof compounds 10 and 11 yields a compound 12 corresponding to a methineyellow colorant.

[0038] Methine dyes and pigments represent an important class ofchromogen in virtually every area requiring a yellow to cyan hue.Numerous derivatives have been made and have been used to make manytypes of dyes (e.g., dispersed, acid, reactive, etc.). Some shortcomingsof prior art methine dyes in hot melt wax systems (i.e., phase changeink systems) are due to solubility and blooming problems. These arisefrom the relatively small and compact structure of prior art methinedyes. Because of their Structures, aggregation of dye moieties readilytakes place. Such aggregation can lead to solubility problems(aggregated molecules can combine and form precipitates which canadversely affect printhead performance), as well as to blooming if theunaggregated molecules migrate to the surface of a printed image.

[0039] An advantage of the present invention is that it encompassessynthetic methods which can be utilized to create methine colorantswhile overcoming the manufacturing and preparation disadvantagesassociated with prior art methine dye preparation (i.e., the use ofhazardous and/or volatile solvents and elaborate purificationprocedures). Specifically, reactions of the present invention arepreferably run without traditional volatile organic solvents. Instead,the reactions are preferably run at temperatures that allow eachcomponent, each intermediate, and each final product to be molten.Accordingly, the reaction mixture functions as its own solvent, and noadditional solvents are needed. Suitably high temperatures are employedto keep the reaction molten during its duration, as well as to allowwater and/or low molecular weight alcohols to be removed. Example 1describes an exemplary colorant preparation procedure encompassed by thepresent invention. The colorant obtained from the process of Example 1has a viscosity similar to the desired viscosity of a final ink, andcould, accordingly, be utilized as ink directly, rather than beingutilized in combination with a carrier. However, the colorant was testedfor suitability in phase change ink applications by combining thecolorant with a phase change ink carrier solution. Specifically, thecolorant was combined with an ink base, filtered and printed (seeExample 2 for preparation of the ink base, and Example 3 for combinationof the colorant and ink base).

[0040] The method described above with reference to compounds 10-12utilized a cyanoacetate derivative having an alkyl chain with at least13 carbon atoms incorporated therein (compound 11). Another methodencompassed by the present invention is to utilize a cyanoacetatederivative which does not have the alkyl chain with at least 13 carbonatoms already incorporated therein, but which can be subsequentlyreacted to incorporate an alkyl group having at least 13 carbon atoms.For instance, the compound 10 which was discussed above can be reactedwith a second compound 13, to form a third compound 14.

[0041] Compound 14 can be subsequently reacted with NH₂(CH₂)_(n)CH₃ toform the compound 12 that was discussed above. While the invention isnot limited by the process order for introducing the alkyl groupfeature, a specific advantage of the invention can be to prepare a newcolorant through solventless transformation in a molten state.

[0042] An exemplary material for compound 10 is shown below as compound15.

[0043] The components R₅₆, R₅₇, R₅₈, and R₅₉ of compound 10 can, forexample, be selected from the group consisting of hydrogen, halogens,hydroxy groups, alkoxy groups, trifluoromethyl groups, and alkyl groups,and can be the same as one another or different than one another. Thecomponents R₇ and R₈ of compound 15 are selected from the groupconsisting of hydrogen and carbon-containing materials, and can be, forexample, alkyl moieties, aryl moieties or hydrogen. Components R₇ and R₈can be the same or different relative to one another, and can becomprised by a common ring. In particular embodiments, at least one ofR₇ and R₈ comprises a chain having the formula of material 5, wherein jis an integer from 0 to about 300, and wherein Q is hydrogen or CH₃, andcan vary between hydrogen and CH₃ within the chain to yield blockco-polymers.

[0044] Another composition which can be formed by methodology similar tothat shown in FIG. 1 is compound 6 (below). An exemplary materialencompassed by the formula of compound 6 can be formed by themethodology shown in FIG. 2.

[0045] The components R₆₀, R₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉,R₇₀, and R₇₁ of compound 6 can, for example, be selected from the groupconsisting of hydrogen, halogens, hydroxy groups, alkoxy groups,trifluoromethyl groups, and alkyl groups, and can be the same as oneanother or different than one another. The components R₁₀, R₁₁, R₁₂,R₁₃, R₁₄ and R₁₅ of compound 6 are selected from the group consisting ofhydrogen and carbon-containing materials, and can be, for example, alkylmoieties, aryl moieties or hydrogen. Components R₁₀, R₁₁, R₁₂, R₁₃, R₁₄and R₁₅ can be the same or different relative to one another. Inparticular embodiments, at least one of the groups R₁₀, R₁₁, R₁₂, R₁₃,R₁₄ and R₁₅ comprise a chain having the formula of material 5. Thelabels “a”, “b”, and “c” of compound 6 are integers of from 1 to 300,and preferably from 1 to 100, and more preferably of from 1 to 10, andcan be the same or different from one another.

[0046] The FIG. 2 reaction scheme shows a method of forming an exemplarycompound 6 having “a”, “b” and “c” equal to 2, and R₆₀-R₇₁ as hydrogen.The resulting compound has a significant amount of hydrophobic characterdue to the three carbon tethers (which are linked in the common startingmaterial tris-triethylamino amine, and joined with a common nitrogenmolecule). (The term “tether” is used herein to refer to an organiclinkage between two components.) Compound 6 is an exemplary compound ofthe present invention. Materials other than compound 6 can be formed bysubstituting other molecules for the tris-triethylamino amine of FIG. 2.Such other molecules can comprise longer carbon chains thantris-triethylamino amine, and more than the three tethers oftris-triethylamino amine. Also, the nitrogen nucleophiles of thetris-triethylamino amine can be replaced with other nucleophiles (suchas, for example, oxygen or sulfur), such that one or more of the amidelinkages shown in compound 6 is replaced by a different type of linkage(such as, for example, an ester or a thioester). Additionally, thecentral amine of triethylamino amine can be replaced with a differentatom, such as, for example carbon. A starting material that can besubstituted for the tris-triethylamino amine, and which comprises acentral carbon atom instead of the central nitrogen oftris-triethylamino amine, is a T-SERIES JEFFAMINE™ (available fromHuntsman Chemical of Austin, Tex.). Another exemplary starting materialwhich could be substituted for tris-triethylamino amine is polyethyleneimine, TETRONIC™ (available from BASF Corporation of Parsippany, N.J.).Yet another exemplary starting material is a material comprising acombination of two or more of T-SERIES JEFFAMINE™, polyethylene imine,and tris-triethylamino amine.

[0047] In light of the above-discussed substitutions for thetris-triethylamino amine utilized during formation of compound 6, itwill be recognized that compound 6 is but one representative of a classof compounds encompassed by the present invention. Such class comprisesat least two segments having the formula 20 shown below, with the atleast two segments being joined through a common central atom ormulti-atom structure. If the at least two segments are joined through acommon atom, such atom can be either carbon, sulfur, phosphorus ornitrogen. In segment 20, R₂₀ and R₂l comprise one or both of carbon andhydrogen; Z₅ comprises carbon, nitrogen, oxygen or sulfur; thecomponents R₇₃, R₇₄, R₇₅, and R₇₆ can, for example, be selected from thegroup consisting of hydrogen, halogens, hydroxy groups, alkoxy groups,trifluoromethyl groups, and alkyl groups, and can be the same as oneanother or different than one another; and b is an integer of from 1 to300, and preferably of from 2 to 20. Another way of describing acompound having at least two segments 20 is shown as compound 21(below), wherein G corresponds to a common central atom or multi-atomstructure that joins the segments,. wherein Z₅, b, R₂₀ and R₂₁ can bethe same or different at different segments within the compound, andwherein d is at least 2. In particular embodiments, a compound of thepresent invention has at least three segments having the formula 20, andaccordingly, d of compound 21 is an integer that is at least 3.

[0048] It is noted that compound 6 can be reacted with organic acids,mineral acids, or combinations of organic and mineral acids, toprotonate one or more of the amines and accordingly form ion pairscomprising the protonated compounds and negative counterions. Exemplaryacids are stearic acid, hydrochloric acid, sulfuric acid, and dodecylbenzene sulfonic acid. The ion pairs formed from compound 6 and theacids can constitute colorants having high molecular weights and desirednon-blooming, non-migrating properties in phase change inks. This aspectof the invention can provide a route to materials which exhibitsolubilized pigment behavior.

[0049] The above-described materials (materials 1-6, 10-15, 20 and 21)can be utilized as colorants in phase change inks. Accordingly, thematerials can be combined with a phase change ink carrier to form aphase change ink composition. Preferably, the materials will be presentin the ink composition to a concentration of from about 0.5% to about60%, and most preferably between 5% and 30%. In the particular caseswherein the colorants have appropriate viscosity and melting temperatureto provide printable properties at a printhead operating temperature, aphase change ink can consist essentially of the colorant (i.e., thephase change ink will be essentially pure colorant, and accordingly haveno carrier).

[0050] The methods described above with reference to FIGS. 1 and 2 areexemplary methods for forming compounds encompassed by the presentinvention. Another exemplary method is shown in FIG. 3. Specifically,FIG. 3 shows that a first compound “A” (which has a carbonyl attached toa leaving group X) is reacted with a second compound “B” (which has acomponent Z bonded to a carbon-containing group R₂) to form a thirdcompound “C”. In particular aspects of the invention, the group R₂ cancomprise an alkyl chain having at least 13 carbon atoms. In otherembodiments, the group R₂ can comprise a component suitable forsubsequent bonding with an alkyl group having at least 13 carbon atoms.The reaction effectively substitutes group X with the group ZR₂. Thegroup X can comprise, for example, O(CH₂)_(m)CH₃, with m being aninteger of from 0 to 10. Preferably, m is an integer of from 0 to 2. Thecomponent Z can comprise, for example, a nucleophile, such as oxygen,sulphur or nitrogen. In particular embodiments of the invention, thematerial Z—R₂ comprises either of compounds 7 or 8, with n an y beingintegers which are preferably at least 12.

NH₂(CH₂)_(n)CH₃   7.

[0051]

[0052] In a further particular embodiment, compound “A” of FIG. 3 cancomprise the carbocation shown below as compound 9.

[0053] The components R₈₀, R₈₁, R₈₂, R₈₃, R₈₄, R₈₅, R₈₆, R₈₇, R₈₈, andR₈₉ of compound 9 can, for example, be selected from the groupconsisting of hydrogen, halogens, hydroxy groups, alkoxy groups,trifluoromethyl groups, and alkyl groups, and can be the same as oneanother or different than one another. The components R₃, R₄, R₅ and R₆of compound 9 can be selected from the group consisting of hydrogen andcarbon-containing materials, and can be, for example, alkyl moieties,aryl moieties or hydrogen. Further, the groups R₃, R₄, R₅ and R₆ ofcompound 9 can be the same or different than one another.

[0054] The reaction of FIG. 3 can comprise, for example, analkylamino-de-alkoxylation reaction which is utilized to add a carbonchain (such as, for example, a stearyl group) to a chromophore. Theaddition of a suitable carbon chain can form a colorant having improvedproperties for utilization in a phase change ink relative to thestarting chromophore. For instance, the addition of a suitable carbonchain can form a colorant having increased molecular weight, enhancedsolubility in an ink base (decreasing the blooming tendency) anddecreased tendency to migrate, relative to the starting chromophore.

[0055] An exemplary chromophore which can be treated byalkylamino-de-alkoxylation is INTRATHERM YELLOW P-346™, available fromCrompton and Knowles. INTRATHERM YELLOW P-346™ provides a bright yellowcolor when formulated into phase change ink bases. In addition, the dyeshows good lightfastness and good thermal stability compared toconventional yellow colorants. Unfortunately, at dye loads much above 1%the dye has a tendency to “bloom” to the surface of a test print. Inaddition, the dye tends to migrate under tape and lamination media. Analkylamino-de-alkoxylation transformation encompassed by the presentinvention can improve the performance of INTRATHERM YELLOW P-346™ inphase change inks. For instance, Example 4 (below), together with thedata following Example 4, shows that modification of INTRATHERM YELLOWP-346™ in accordance with the present invention can enhance the imagestability of printed phase change test images relative to unmodifiedINTRATHERM YELLOW P-346™. Further, although the example modification isrelative to INTRATHERM YELLOW P-346™, the procedure of the presentinvention can be readily utilized on a large number of chromophores toenhance their solubility and migration fastness in phase change inks,and accordingly, the commercialization potential of such chromophores issignificantly increased. This feature of the invention is alsoapplicable for the preparation of solvent soluble colorants from dyestypically insoluble in organic carriers.

[0056] Exemplary embodiments of the present invention are described inthe Examples below. It is to be understood, however, that the Examplesare provided for illustration purposes only. The invention is to belimited only by the claims which follow, and not by the chemistry shownin the following Examples except to the extent that such chemistry isexpressly recited in the following claims.

EXAMPLE 1

[0057] Octadecyl amine¹ (about 135.9 grams (0.505 moles)) was carefullyheated in a one-liter four-neck resin kettle equipped with a Truborestirrer, thermocouple-temperature controller, N₂ atmosphere, and vacuumadapter to about 80°C., at which time it became molten and agitation wasbegun. Once the octadecyl amine was molten, about 50.0 grams (0.505moles) of methyl cyanoacetate² was slowly added. When the addition wascomplete, the temperature was held at about 90°C. for approximately 45minutes and then slowly raised to about 150°C. After about one hour atabout 150°C., the N₂ atmosphere was removed and a vacuum was applied.After about one hour, the vacuum was removed, the N₂ atmosphere wasre-established, and the temperature was lowered to about 135°C. When thetemperature reached about 135°C., about 71.5 grams (0.480 moles) ofdimethylaminobenzaldehyde³ were added and heated, under N₂, for aboutone hour. The N₂ atmosphere was then removed, the temperature wasincreased to about 150°C., and a vacuum was applied. After about onehour, the vacuum was removed and the reaction product was poured intoaluminum pans and allowed to cool and solidify. The final product was ayellow solid at room temperature. A sample of the final product wasdissolved in toluene, and was determined to have a spectral strength ofabout 69,560 (milliliters * Absorbance Units/gram) at a lambda_(max) of407 nm. The spectral strength was measured using a Perkin Elmer Lambda2S UV/VIS spectrophotometer.

EXAMPLE 2

[0058] About 600.0 grams of stearyl stearamide⁴, about 432.0 grams(1.674 moles) of octylphenol ethoxylate⁵, about 252.0 grams (0.696moles) of hydroabietyl alcohol⁶, and about 273.0 grams (0.52) moles ofC-32 linear alcohol⁷ were mixed in a 3L four-neck resin kettle equippedwith a Trubore stirrer, N₂ atmosphere, addition funnel (200 mL), andthermocouple-temperature controller. This mixture was heated to 125°C.and agitation begun when all components were molten (at approximately100°C.). To the mixture, and about 334.2 grams (1.505 moles) ofisophorone diisocyanate⁸ was added over approximately five minutesthrough the addition funnel. About 0.66 grams of dibutyltindilaurate⁹was added and the reaction mixture heated to about 150°C. After abouttwo hours at about 150°C., additional amounts of about 45.0 grams (0.174moles) of octylphenol ethoxylate, about 45.0 grams (0.124 moles) ofhydroabietyl alcohol, about 45.0 grams (0.086 moles) of C-32 linearalcohol, and about 0.05 grams of dibutyltindilaurate were added and thereaction mixture maintained at about 150°C. for about two hours. AFourier transform infrared spectrum (FT-IR spectrum) of the reactionproduct was obtained to insure that all of the isocyanate functionalitywas consumed. The absence (disappearance) of a peak at ˜2285 cm⁻¹ (NCO)and the appearance (or increase in magnitude) of peaks at ˜1740-1680cm⁻¹ and ˜1540-1530 cm⁻¹ corresponding to urethane frequencies were usedto confirm this. The final mixed urethane product was then poured intoaluminum molds and allowed to cool and harden. The resulting product wasa solid at room temperature and characterized by a viscosity of about14.92 cPs as measured by a Ferranti-Shirley cone-plate viscometer atabout 140°C.

EXAMPLE 3

[0059] About 345.0 grams of the material from Example 2, about 125.0grams of Lawter SA-3850 (Lawter International, Inc. or Northbrook,Ill.), and about 10.0 grams of the yellow colorant from Example 1 werecombined in a one-liter stainless steel beaker. The materials weremelted together at a temperature of about 125°C. in an oven, thenblended by stirring in a temperature controlled mantle at about 125°C.for about one-half hour to form a yellow ink. The yellow ink wasfiltered through a heated Mott apparatus (available from MottMetallurgical) using a 2 micron filter and a pressure of about 15 psi.The filtered phase change ink was poured into molds and allowed tosolidify to form ink sticks. The final ink product had a viscosity ofabout 11.44 cPs as measured by a Ferranti-Shirley cone-plate viscometerat about 140°C. The product had a spectral strength of 1400(milliliters * Absorbance Units/gram) at a lambda_(max) of 407 nm whendissolved in toluene. The spectral strength was measured using a PerkinElmer Lambda 2S UV/VIS spectrophotometer.

[0060] The ink was tested in a Tektronix PHASER™ 340 printer (which usesan offset transfer printing system), and was found to provide images ofgood color, print quality and durability.

EXAMPLE 4

[0061] A 100 mL one-neck flask was equipped with a magnet and placed ina silicone oil bath on a hot plate/magnetic stirrer. The flask wasequipped with a vacuum adapter and configured to be filled with an N₂atmosphere. About 10.0 grams of stearyl amine¹⁰ and about 12.5 gramsINTRATHERM YELLOW P346™¹¹ were mixed in the flask. The mixture washeated to about 95°C. in an N₂ atmosphere, at which time it becamemolten and agitation was begun. After about 0.5 hours at about 95°C.,the temperature was increased to about 105°C. and held for approximatelyfour hours. Bubbles were observed evolving from the reaction mixture forseveral hours. The temperature was then increased to about 110°C. andheld for about six hours. The N₂ addition was then stopped, a vacuum wasintroduced to the reaction vessel, and the temperature was maintained atabout 110°C. After about 30 minutes, the vacuum was removed, N₂reintroduced, about 80 mL of toluene was added, and the reaction mixtureallowed to cool to room temperature with stirring.

[0062] The reaction product in toluene was then poured into a 600 mLcoarse frit Buchner funnel containing a toluene slurry of silica gel¹²and attached to a 1-liter vacuum flask. About 500 mL of toluene waseluted through the silica gel and subsequently removed via rotaryevaporation. This toluene elution step was repeated two additionaltimes, and a final time with acetone. A total of four 500 mL fractionswere collected and concentrated. Thin layer chromatography (TLC) onreversed phase plates of the four fractions was performed (usingmethanol as an eluent) and simultaneously compared with the startingdye. The third fraction showed the highest percentage of the desired,purified product. The purified reaction product (referred to hereafteras stearyl-modified INTRATHERM YELLOW P-346™) was a deep orange wax. Thespectral strength of the purified product was determined in toluene tobe 33,400 (milliliters * Absorbance Units/gram) at 414 nm. The peakwidth at half height was determined to be 110 nm.

Image Stability Characterization of the Stearyl-Modified INTRATHERMYELLOW P-346™

[0063] Two inks were prepared utilizing a common phase change inkcarrier. The only difference between the two inks was that one of theinks used INTRATHERM YELLOW P-346™ as a colorant, and the other ink usedthe stearyl-modified INTRATHERM YELLOW P-346™ of Example 4 as acolorant. The dye proportions in the two inks were adjusted to normalizethe spectral strength. The two inks were printed on a PHASER™ 600printer and the relative performance of the inks was compared by severaltest methods. Results of these tests are tabulated below.

A. Color Print Test

[0064] The ink comprising stearyl-modified INTRATHERM YELLOW P-346™ as acolorant gave a slightly reddish yellow solid fill of high chromaticity.The color space was determined and is listed below in Table 1. TABLE 1COLOR L* a* b* Cyan 50.66 −19.91 −42.91 Magenta 49.48 73.53 −20.17Yellow 82.00 3.12 94.73 Black 24.12 0.81 −0.44 Red 46.51 58.15 39.39Green −38.91 24.47 11.2 Blue 26.44 28.97 −44.38

B. Diffusion

[0065] The extent of dye diffusion was determined by using the CIELABcolor-difference formula¹³ for measurements of the same test panelbefore and after aging 72 hours in a 45°C. oven. The resulting colordifference values (ΔE) are summarized in Table 2, which lists diffusionobserved for two types of prints: unlaminated and laminated. Test panelscontaining small amounts of the diffusing color surrounded by largeamounts of a second color have been observed to be most sensitive to dyediffusion. The proportion of the primary process colors in each testpanel is shown in column 1 of Table 2. Data obtained utilizingcommercially available INTRATHERM YELLOW P-346™ is listed under thecategory “Unmodified” in Table 2, and data obtained from thestearyl-modified INTRATHERM YELLOW P-346™ of Example 4 is listed underthe category “Modified” in Table 2. The data in Table 2 show that thestearyl-modified INTRATHERM YELLOW P-346™ has about a 56% improvementwhen unlaminated, and about a 28% improvement when laminated relative totest panels containing unmodified INTRATHERM YELLOW P-346™. TABLE 2DIFFUSION TEST RESULTS (ΔE, relative to initial color measurement) TestPanel Composition Unlaminated Laminated C/M/Y Unmodified ModifiedUnmodified Modified 20/0/0 0.3 0.1 n/a* 0.3 20/100/0 1.8 0.8 2.6 2.920/0/100 1.6 1.6 1.6 1.4 100/20/0 5.4 5.7 n/a* 3.0 0/20/0 1.5 1.0 4.12.5 0/20/100 6.4 3.8 3.4 2.1 100/0/20 19.5 10.0 n/a* 14.3 0/100/20 14.38.5 16.2  11.7 0/0/20 2.7 0.5 24.9  18.3

C. Blooming

[0066] Blooming was tested by placing a printed solid fill image in a60°C. oven for seven days. Prior to placement in the oven, the bottomsection of the image was impressed with fingerprint nil. In addition, astrip of transparent tape was placed across the lower margin. Bloomingcould be observed in the sample comprising commercially available (i.e.,unmodified) INTRATHERM YELLOW P-346™ after seven days, whereas thesample comprising stearyl-modified INTRATHERM YELLOW P-346™ did notexhibit significant blooming after the same period of time. In addition,a white facial tissue could be gently wiped across the sample comprisingunmodified INTRATHERM YELLOW P-346™. This was not observed whenperformed with the sample comprising stearyl-modified INTRATHERM YELLOWP-346™.

D. Carryover of Sublimation onto Facing Sheet

[0067] The samples utilized for the blooming test (described above) werealso utilized for testing carryover of sublimation onto a facing sheet.An unprinted sheet was provided over and in facing relation to thesamples. Examination of the facing sheet revealed a noticeable migrationof yellow dye from the sample comprising unmodified INTRATHERM YELLOWP-346™ after seven days at 60°C., and revealed no migration of yellowdye from the sample comprising stearyl-modified INTRATHERM YELLOWP-346™.

E. Tape Diffusion

[0068] Printed samples comprising stearyl-modified INTRATHERM YELLOWP-346™ were compared to printed samples comprising unmodified INTRATHERMYELLOW P-346™ for diffusion under transparent tape. Such comparisonshowed that the samples comprising stearyl-modified INTRATHERM YELLOWP-346™ had about a 50% improvement relative to the samples comprisingstearyl-modified INTRATHERM YELLOW P-346™ (i.e., less colorantmigration), as determined by visual inspection.

1. A compound having the formula:

wherein R₁, Z and the carbonyl can be comprised by a common ring,wherein R₁ comprises a chromophore that absorbs light from the visiblewavelength range; wherein the segment Z comprises one or more of C, O, Nand S; and wherein n is an integer that is at least
 12. 2. The compoundof claim 1 wherein n is at least 17 and not more than
 299. 3. Thecompound of claim 1 wherein the segment Z(CH₂)_(n)CH₃ is NH(CH₂)_(n)CH₃.4. The compound of claim 1 wherein the segment Z(CH₂)_(n)CH₃ isCH₃(CH₂)_(n)—N—(CH₂)_(y)CH₃ wherein y is an integer of from 0 to 300,and can be the same or different than n.
 5. The compound of claim 1wherein the R₁ and the carbonyl together comprise a chemical groupselected from the group consisting of ester, lactone, amide, lactam, andimide.
 6. The compound of claim 1 having the formula

wherein R₅₀, R₅₁, R₅₂, and R₅₃ are selected from the group consisting ofhydrogen, halogens, hydroxy groups, alkoxy groups, trifluoromethylgroups, and alkyl groups, and can be the same as one another ordifferent than one another; and wherein at least one of R₇ and R₈comprises a chain having the formula,

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 7. The compound of claim 1 having the formula

wherein at least one of R₇ and R₈ comprises a chain having the formula,

wherein j is an integer from 0 to about 300, wherein the representationof “(Q H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 8. The compound of claim 1 having the formula

wherein R₈₀, R₈₁, R₈₂, R₈₃, R₈₄, R₈₅, R₈₆, R₈₇, R₈₈, and R₈₉ areselected from the group consisting of hydrogen, halogens, hydroxygroups, alkoxy groups, trifluoromethyl groups, and alkyl groups, and canbe the same as one another or different than one another; and whereinR₃, R₄, R₅ and R₆ comprise carbon and can be the same or different thanone another.
 9. The compound of claim 1 having the formula

wherein R₃, R₄, R₅ and R₆ comprise carbon and can be the same ordifferent than one another.
 10. A compound having the formula:

wherein R₆₀, R₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, and R₇₁are selected from the group consisting of hydrogen, halogens, hydroxygroups, alkoxy groups, trifluoromethyl groups, and alkyl groups, and canbe the same as one another or different than one another; wherein Dcomprises carbon, sulphur, phosphorus or nitrogen; wherein R₁₀, R₁₁,R₁₂, R₁₃, R₁₄ and R₁₅ comprise at least one of carbon or hydrogen, andcan be the same or different than one another; wherein Z₁, Z₂ and Z₃ canbe the same or different than one another and comprise S, O, C or N; andwherein a, b and c can be the same or different than one another and areintegers that are at least
 1. 11. The compound of claim 10 wherein R₆₀,R₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, and R₇₁ are hydrogen.12. The compound of claim 10 wherein D is nitrogen, and is in a cationicform.
 13. The compound of claim 10 wherein at least one of R₁₀, R₁₁,R₁₂, R₁₃, R₁₄ and R₁₅ comprises a chain having the formula

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 14. The compound of claim 10 wherein each of R₁₀, R₁₁,R₁₂, R₁₃, R₁₄ and R₁₅ comprises a chain having the formula

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 15. The compound of claim 10 wherein each of Z₁, Z₂and Z₃ is NH.
 16. A compound comprising at least two segments of theformula shown below joined to one another through a common atom ormulti-atom structure:

wherein R₇₃, R₇₄, R₇₅, and R₇₆ are selected from the group consisting ofhydrogen, halogens, hydroxy groups, alkoxy groups, trifluoromethylgroups, and alkyl groups, and can be the same as one another ordifferent than one another; wherein R₂₀, R₂₁ comprise at least one ofcarbon or hydrogen, and can be the same or different than one another;wherein Z₅ comprises at least one of C, S, O or N; wherein b comprisesan integer that is at least 1; the integer b being the same or differentamongst the different segments; Z₅ being the same or different amongstthe different segments; and the groups R₂₀ and R₂₁ being the same ordifferent amongst the different segments.
 17. The compound of claim 16wherein R₇₃, R₇₄, R₇₅, and R₇₆ are hydrogen.
 18. The compound of claim16 wherein the compound comprises at least three of the segments havingthe shown formula.
 19. The compound of claim 16 wherein the at least twosegments are joined through a common atom, said common atom being eithercarbon, sulfur, phosphorus or nitrogen.
 20. A solid phase change inkcomposition consisting essentially of a colorant having the formula:

wherein R₁, Z and the carbonyl can be comprised by a common ring,wherein said colorant comprises a chromophore that absorbs light fromthe visible wavelength range, wherein the segment Z comprises one ormore of carbon, oxygen, sulfur and nitrogen, and wherein n is an integerthat is at least
 12. 21. A solid phase change ink composition,comprising: a phase change ink carrier; and a colorant having theformula:

wherein R₁, Z and the carbonyl can be comprised by a common ring,wherein said colorant comprises a chromophore that absorbs light fromthe visible wavelength range, wherein the segment Z comprises one ormore of carbon, oxygen, sulfur and nitrogen, and wherein n is an integerthat is at least
 12. 22. The phase change ink of claim 21 wherein n isat least 17 and not more than
 299. 23. The phase change ink of claim 21wherein Z is O, NH or S.
 24. The phase change ink of claim 21 whereinthe segment Z(CH₂)_(n)CH₃ is NH(CH₂)_(n)CH₃.
 25. The phase change ink ofclaim 21 wherein the segment Z(CH₂)_(n)CH₃ isCH₃(CH₂)_(n)—N—(CH₂)_(y)CH₃ wherein y is an integer of from 0 to 300,and can be the same or different than n.
 26. The phase change ink ofclaim 21 wherein the R₁ and the carbonyl together comprise a chemicalgroup selected from the group consisting of ester, lactone, amide,lactam, and imide.
 27. The phase change ink of claim 21 wherein thecolorant has the formula

wherein R₅₀, R₅₁, R₅₂, and R₅₃ are selected from the group consisting ofhydrogen, halogens, hydroxy groups, alkoxy groups, trifluoromethylgroups, and alkyl groups, and can be the same as one another ordifferent than one another; wherein at least one of R₇ and R₈ comprisesa chain having the formula,

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 28. The phase change ink of claim 27 wherein R₅₀, R₅₁,R₅₂, and R₅₃ are hydrogen.
 29. The phase change ink of claim 21 whereinthe colorant has the formula

wherein R₈₀, R₈₁, R₈₂, R₈₃, R₈₄, R₈₅, R₈₆, R₈₇, R₈₈, and R₈₉ areselected from the group consisting of hydrogen, halogens, hydroxygroups, alkoxy groups, trifluoromethyl groups, and alkyl groups, and canbe the same as one another or different than one another; wherein R₃,R₄, R₅ and R₆ comprise carbon and can be the same or different than oneanother.
 30. The phase change ink of claim 29 wherein R₈₀, R₈₁, R₈₂,R₈₃, R₈₄, R₈₅, R₈₆, R₈₇, R₈₈, and R₈₉ are hydrogen.
 31. A solid phasechange ink composition, comprising: a phase change ink carrier; and acolorant having at least two segments of the formula shown below joinedto one another through a common atom or multi-atom structure:

wherein R₇₃, R₇₄, R₇₅, and R₇₆ are selected from the group consisting ofhydrogen, halogens, hydroxy groups, alkoxy groups, trifluoromethylgroups, and alkyl groups, and can be the same as one another ordifferent than one another; wherein said colorant comprises achromophore that absorbs light from the visible wavelength range;wherein R₂₀, R₂₁ comprise at least one of carbon or hydrogen, and can bethe same or different than one another; wherein Z₅ comprises at leastone of C, S, O or N; and wherein b comprises an integer that is at least1; the integer b being the same or different amongst the differentsegments; Z₅ being the same or different amongst the different segments;and the groups R₂₀ and R₂₁ being the same or different amongst thedifferent segments.
 32. The phase change ink of claim 31 wherein R₇₃,R₇₄, R₇₅, and R₇₆ are hydrogen.
 33. The phase change ink of claim 31wherein the at least two segments are joined through a common atom, saidcommon atom being either carbon, phosphorus, sulfur or nitrogen.
 34. Asolid phase change ink composition consisting essentially of a coloranthaving the formula:

wherein R₆₀, R₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, and R₇₁are selected from the group consisting of hydrogen, halogens, hydroxygroups, alkoxy groups, trifluoromethyl groups, and alkyl groups, and canbe the same as one another or different than one another; wherein saidcolorant comprises a chromophore that absorbs light from the visiblewavelength range; wherein R₁₀, R₁₁, R₁₂, R₁₃, R₁₄ and R₁₅ comprise atleast one of carbon or hydrogen, and can be the same or different thanone another; wherein D comprises carbon, sulphur, phosphorus ornitrogen, wherein Z₁, Z₂ and Z₃ can be the same or different than oneanother and comprise S, O, C or N; and wherein a, b and c can be thesame or different than one another and are integers that are at least 1.35. The phase change ink of claim 34 wherein R₆₀, R₆₁, R₆₂, R₆₃, R₆₄,R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, and R₇₁ are hydrogen.
 36. A solid phasechange ink composition, comprising: a phase change ink carrier; and acolorant having the formula:

wherein R₆₀, R₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, and R₇₁are selected from the group consisting of hydrogen, halogens, hydroxygroups, alkoxy groups, trifluoromethyl groups, and alkyl groups, and canbe the same as one another or different than one another; wherein saidcolorant comprises a chromophore that absorbs light from the visiblewavelength range; wherein R₁₀, R₁₁, R₁₂, R₁₃, R₁₄ and R₁₅ comprise atleast one of carbon or hydrogen, and can be the same or different thanone another; wherein D comprises carbon, sulphur, phosphorus ornitrogen, wherein Z₁, Z₂ and Z₃ can be the same or different than oneanother and comprise S, O, C or N; and wherein a, b and c can be thesame or different than one another and are integers that are at least 1.37. The phase change ink of claim 36 wherein R₆₀, R₆₁, R₆₂, R₆₃, R₆₄,R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, and R₇₁ are hydrogen.
 38. The phase changeink of claim 36 wherein D is a cationic form of nitrogen and accordinglyhas a positive charge, and further comprising a negative ion paired withthe positively charged D.
 39. The phase change ink of claim 36 wherein Dis a cationic form of nitrogen and accordingly has a positive charge,and further comprising a negative ion paired with the positively chargedD, the negative ion being a halogen.
 40. The phase change ink of claim36 wherein D is a cationic form of nitrogen and accordingly has apositive charge, and further comprising a negative ion paired with thepositively charged D, the negative ion being deprotonated dodecylbenzene sulfonic.
 41. The phase change ink of claim 36 wherein at leastone of R₁₀, R₁₁, R₁₂, R₁₃, R₁₄ and R₁₅ comprises a chain having theformula

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 42. The phase change ink of claim 36 wherein each ofR₁₀, R₁₁, R₁₂, R₁₃, R₁₄ and R₁₅ comprises a chain having the formula

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 43. The phase change ink of claim 36 wherein each ofZ₁, Z₂ and Z₃ is NH.
 44. A method of forming a colorant comprisingreacting a first compound having the formula,

with a second compound having the formula Z(CH₂)_(n)CH₃, wherein n is aninteger that is at least 12, to form a third compound having theformula,

wherein the third compound comprises a chromophore that absorbs lightfrom the visible wavelength range.
 45. The method of claim 44 wherein nis at least 17 and not more than
 299. 46. The method of claim 44 whereinZ is selected from the group consisting of carbon, oxygen, sulphur andnitrogen.
 47. The method of claim 44 wherein the structure Z(CH₂)_(n)CH₃is NH₂(CH₂)_(n)CH₃.
 48. The method of claim 44 wherein the structureZ(CH₂)_(n)CH₃ is

wherein y is an integer of from 0 to 300, and can be the same ordifferent than n.
 49. The method of claim 44 wherein X is O(CH₂)_(m)CH₃,and wherein m is an integer of from 0 to
 10. 50. The method of claim 44wherein the R₁ and the carbonyl together comprise a chemical groupselected from the group consisting of ester, lactone, amide, lactam, andimide.
 51. The method of claim 44 wherein the R₁ and the carbonyltogether comprise an auxochrome.
 52. The method of claim 44 wherein theR₁ comprises an auxochrome.
 53. The method of claim 44 wherein thechromophore comprises at least a segment selected from the groupconsisting of methine, metal phthalocyanine, azamethine, azo,triphenylmethane, rhodamine, xanthene, indoaniline, pyridone, perylene,anthrapyridone and anthraquinone.
 54. The method of claim 44 wherein thefirst compound is

wherein R₈₀, R₈₁, R₈₂, R₈₃, R₈₄, R₈₅, R₈₆, R₈₇, R₈₈, R₈₉ are selectedfrom the group consisting of hydrogen, halogens, hydroxy groups, alkoxygroups, trifluoromethyl groups, and alkyl groups, and can be the same asone another or different than one another; wherein R₃, R₄, R₅ and R₆comprise carbon and can be the same or different than one another. 55.The method of claim 54 wherein R₈₀, R₈₁, R₈₂, R₈₃, R₈₄, R₈₅, R₈₆, R₈₇,R₈₈, and R₈₉ are hydrogen.
 56. A method of forming a colorantcomprising: providing a first compound having the formula

wherein A is an aromatic ring and R₄ comprises one or both of carbon andhydrogen, and wherein said first compound comprises a chromophore thatabsorbs light from the visible wavelength range; and reacting said firstcompound with a second compound having the formula

to form a third compound having the formula

wherein n is an integer that is at least
 12. 57. The method of claim 56wherein n is at least 17 and not more than
 299. 58. The method of claim56 wherein the second compound comprises stearyl cyanoacetate, stearylcyanoacetamide, or a mixture of stearyl cyanoacetate and stearylcyanoacetamide.
 59. The method of claim 56 wherein the first compound is

wherein R₅₆, R₅₇, R₅₈, and R₅₉ are selected from the group consisting ofhydrogen, halogens, hydroxy groups, alkoxy groups, trifluoromethylgroups, and alkyl groups, and can be the same as one another ordifferent than one another; and wherein R₇ and R₈ can be the same ordifferent than one another, can be comprised by a common ring, and areselected from the group consisting of H and carbon-containing materials.60. The method of claim 59 wherein R₅₆, R₅₇, R₅₈, and R₅₉ are hydrogen.61. The method of claim 59 wherein at least one of R₇ and R₈ comprises achain having the formula,

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.
 62. A method of forming a colorant comprising:providing a first compound having the formula

wherein A is an aromatic ring and R₄ comprises one or both of carbon andhydrogen, and wherein the combination of R₄ and A comprises achromophore that absorbs color in the visible wavelength range; reactingsaid first compound with a second compound having the formula

to form a third compound having the formula;

and reacting said third compound with NH₂(CH₂)_(n)CH₃ to form

wherein n is an integer that is at least
 12. 63. The method of claim 62wherein n is at least 17 and not more than
 299. 64. The method of claim62 wherein the first compound is

wherein R₅₆, R₅₇, R₅₈, and R₅₉ are selected from the group consisting ofhydrogen, halogens, hydroxy groups, alkoxy groups, trifluoromethylgroups, and alkyl groups, and can be the same as one another ordifferent than one another; and wherein R₇ and R₈ can be the same ordifferent than one another, can be comprised by a common ring, and areselected from the group consisting of H and carbon-containing materials.65. The method of claim 64 wherein R₅₆, R₅₇, R₅₈, and R₅₉ are hydrogen.66. The method of claim 64 wherein at least one of R₇ and R₈ comprises achain having the formula,

wherein j is an integer from 0 to about 300, wherein the representationof “(Q, H)” indicates that either a group Q or a hydrogen can be in theshown positions, wherein the group Q is either an alkyl group or an arylgroup, and wherein Q can vary amongst different alkyl and aryl groupswithin the chain.